DE2359386C3 - Verfahren zur Herstellung von Isocyanurat- und Oxazolidonringe enthaltenden Duroplasten - Google Patents
Verfahren zur Herstellung von Isocyanurat- und Oxazolidonringe enthaltenden DuroplastenInfo
- Publication number
- DE2359386C3 DE2359386C3 DE2359386A DE2359386A DE2359386C3 DE 2359386 C3 DE2359386 C3 DE 2359386C3 DE 2359386 A DE2359386 A DE 2359386A DE 2359386 A DE2359386 A DE 2359386A DE 2359386 C3 DE2359386 C3 DE 2359386C3
- Authority
- DE
- Germany
- Prior art keywords
- diisocyanate
- epoxy
- isocyanate
- resin
- resins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 title claims description 14
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 14
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 31
- 150000002513 isocyanates Chemical class 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 23
- 150000002118 epoxides Chemical class 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000002780 morpholines Chemical class 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- 229920000965 Duroplast Polymers 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000004593 Epoxy Substances 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 18
- 229920000647 polyepoxide Polymers 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 11
- CCKWMUGWAKTDIV-UHFFFAOYSA-N 4-(6-morpholin-4-ylhexyl)morpholine Chemical compound C1COCCN1CCCCCCN1CCOCC1 CCKWMUGWAKTDIV-UHFFFAOYSA-N 0.000 description 10
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 10
- 229920003002 synthetic resin Polymers 0.000 description 10
- 239000000057 synthetic resin Substances 0.000 description 10
- 230000004580 weight loss Effects 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- -1 alkali metal halogens Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- QCBSYPYHCJMQGB-UHFFFAOYSA-N 2-ethyl-1,3,5-triazine Chemical compound CCC1=NC=NC=N1 QCBSYPYHCJMQGB-UHFFFAOYSA-N 0.000 description 2
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 2
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 description 2
- ZRQUNTRHHLHXRX-UHFFFAOYSA-N 4-(4-morpholin-4-ylbutyl)morpholine Chemical compound C1COCCN1CCCCN1CCOCC1 ZRQUNTRHHLHXRX-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- 230000003628 erosive effect Effects 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- SIZPGZFVROGOIR-UHFFFAOYSA-N 1,4-diisocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=C(N=C=O)C2=C1 SIZPGZFVROGOIR-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- WXVKGHVDWWXBJX-UHFFFAOYSA-N 3-morpholin-4-ylpropanenitrile Chemical compound N#CCCN1CCOCC1 WXVKGHVDWWXBJX-UHFFFAOYSA-N 0.000 description 1
- ZRIILUSQBDFVNY-UHFFFAOYSA-N 4-dodecylmorpholine Chemical compound CCCCCCCCCCCCN1CCOCC1 ZRIILUSQBDFVNY-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- WUKUJFNYTULCOP-UHFFFAOYSA-N 4-propyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(CCC)CCC2OC21 WUKUJFNYTULCOP-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- VUPOPVGVEARXGA-UHFFFAOYSA-N C[SiH2]C.N=C=O.N=C=O Chemical compound C[SiH2]C.N=C=O.N=C=O VUPOPVGVEARXGA-UHFFFAOYSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- 229910000976 Electrical steel Inorganic materials 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- IUJJPSLPEWPXBV-UHFFFAOYSA-N N=C=O.N=C=O.C(C=C1)=CC=C1[SiH2]C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C(C=C1)=CC=C1[SiH2]C1=CC=CC=C1 IUJJPSLPEWPXBV-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- JSMWYJGCNSFQDN-UHFFFAOYSA-N azonane-2,9-dione Chemical compound O=C1CCCCCCC(=O)N1 JSMWYJGCNSFQDN-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- DNWBGZGLCKETOT-UHFFFAOYSA-N cyclohexane;1,3-dioxane Chemical compound C1CCCCC1.C1COCOC1 DNWBGZGLCKETOT-UHFFFAOYSA-N 0.000 description 1
- XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- XJRAOMZCVTUHFI-UHFFFAOYSA-N isocyanic acid;methane Chemical compound C.N=C=O.N=C=O XJRAOMZCVTUHFI-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4028—Isocyanates; Thioisocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/04—Preparatory processes
- C08G69/06—Solid state polycondensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Manufacture Of Motors, Generators (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47118986A JPS5231000B2 (enrdf_load_stackoverflow) | 1972-11-29 | 1972-11-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2359386A1 DE2359386A1 (de) | 1974-06-20 |
| DE2359386B2 DE2359386B2 (de) | 1980-08-07 |
| DE2359386C3 true DE2359386C3 (de) | 1985-12-05 |
Family
ID=14750165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2359386A Expired DE2359386C3 (de) | 1972-11-29 | 1973-11-28 | Verfahren zur Herstellung von Isocyanurat- und Oxazolidonringe enthaltenden Duroplasten |
Country Status (11)
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5727894B2 (enrdf_load_stackoverflow) * | 1974-10-11 | 1982-06-14 | ||
| JPS5174095A (en) * | 1974-12-25 | 1976-06-26 | Mitsubishi Chem Ind | Okisazoridon isoshianureetofuoomuno seizoho |
| JPS51106002A (en) * | 1975-03-14 | 1976-09-20 | Hitachi Ltd | Denkimakisen no zetsuenshorihoho |
| JPS51115602A (en) * | 1975-04-04 | 1976-10-12 | Hitachi Ltd | Winding of electric machines and apparatuses |
| JPS51121705A (en) * | 1975-04-18 | 1976-10-25 | Hitachi Ltd | Insulated winding of electric machine |
| JPS52112799A (en) * | 1976-03-19 | 1977-09-21 | Hitachi Ltd | Manufacturing method of electrical insulation body |
| JPS52151396A (en) * | 1976-06-11 | 1977-12-15 | Hitachi Chem Co Ltd | Composition for anticorrosive frp |
| JPS53115001A (en) * | 1977-03-17 | 1978-10-07 | Matsushita Electric Ind Co Ltd | Preparing coreless armature |
| JPS53116402A (en) | 1977-03-19 | 1978-10-11 | Hitachi Ltd | Electric insulation device |
| DE2722400C2 (de) * | 1977-05-17 | 1985-05-30 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von wärmebeständigen, blasenfreien Isocyanuratgruppen aufweisenden Kunststoffen |
| CH624968A5 (enrdf_load_stackoverflow) * | 1977-06-14 | 1981-08-31 | Ciba Geigy Ag | |
| EP0035072B1 (de) * | 1980-03-03 | 1984-06-13 | BBC Aktiengesellschaft Brown, Boveri & Cie. | Duroplastisch härtbare lösungsmittelfreie Harzmischung und ihre Verwendung |
| DE3323122A1 (de) * | 1983-06-27 | 1985-05-23 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur herstellung von reaktionsharzformstoffen |
| DE3323084A1 (de) * | 1983-06-27 | 1985-01-10 | Siemens AG, 1000 Berlin und 8000 München | Verfahren zur herstellung von formstoffen |
| GB8412900D0 (en) * | 1984-05-21 | 1984-06-27 | Secr Defence | Thermosetting resin compositions |
| GB8912952D0 (en) * | 1989-06-06 | 1989-07-26 | Dow Rheinmuenster | Epoxy-terminated polyoxazolidones,process for the preparation thereof and electrical laminates made from the epoxy-terminated polyoxazolidones |
| JP3133090B2 (ja) * | 1991-04-03 | 2001-02-05 | 富士電機株式会社 | 突極界磁巻線の絶縁処理方法 |
| DE4223630A1 (de) * | 1992-07-17 | 1994-01-20 | Siemens Ag | Oxazolidinonstrukturen aufweisende präpolymere Epoxidharzmischung |
| JPH0686384U (ja) * | 1993-05-17 | 1994-12-13 | ホシデン株式会社 | 電気コード引出し具 |
| EP1426392B1 (en) * | 2001-08-30 | 2010-02-24 | Mitsubishi Gas Chemical Company, Inc. | Composition for optical material |
| ES2373276B1 (es) * | 2010-07-20 | 2012-12-20 | Universitat Rovira I Virgili | Composición y procedimiento para el entrecruzamiento de una resina epoxi con un isocianato, y material entrecruzado obtenido. |
| EP2841499B1 (en) * | 2012-04-27 | 2016-11-30 | Dow Global Technologies LLC | Curable epoxy resin compositions and composites made therefrom |
| US20150162110A1 (en) * | 2012-06-26 | 2015-06-11 | Dow Global Technologies Llc | Insulating composites for power transmission and distribution |
| BR112015010248A2 (pt) * | 2012-11-07 | 2017-07-11 | Dow Global Technologies Llc | composição de resina epóxi curável, processo para preparar a composição de resina epóxi curável e compósito |
| DE102014226842A1 (de) | 2014-12-22 | 2016-06-23 | Henkel Ag & Co. Kgaa | Katalysator-Zusammensetzung zur Härtung von Epoxidgruppen-haltigen Harzen |
| DE102014226838A1 (de) * | 2014-12-22 | 2016-06-23 | Henkel Ag & Co. Kgaa | Oxazolidinon- und Isocyanurat-vernetzte Matrix für faserverstärktes Material |
| EP3500611B1 (en) | 2016-08-19 | 2021-08-11 | Covestro Intellectual Property GmbH & Co. KG | Process for the synthesis of polyoxazolidinone compounds |
| JP6903899B2 (ja) * | 2016-11-25 | 2021-07-14 | 東ソー株式会社 | 硬質イソシアヌレートフォーム組成物および硬質イソシアヌレートフォームの製造方法 |
| ES3013876T3 (en) * | 2018-05-18 | 2025-04-15 | Dow Global Technologies Llc | A polyisocyanate component, a polyurethane foaming system and an article made therefrom |
| CN117542641B (zh) * | 2023-11-08 | 2024-06-14 | 江苏普隆磁电有限公司 | 一种耐热钕铁硼磁体的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA833619A (en) * | 1970-02-03 | Edward F. Hayash, Jr. | High temperature resistant, low flame spread cellular polymers | |
| DE951168C (de) * | 1953-02-01 | 1956-10-25 | Bayer Ag | Verfahren zur Herstellung von hoehermolekularen Polyisocyanaten |
| US3020262A (en) * | 1957-12-19 | 1962-02-06 | Jefferson Chem Co Inc | Method for producing 2-oxazolidones from epoxides and isocyanates |
| BE593093A (enrdf_load_stackoverflow) * | 1959-09-12 | |||
| US3198551A (en) * | 1961-03-27 | 1965-08-03 | Garner Fay Troy | Pusher vehicle |
| US3206352A (en) * | 1962-03-23 | 1965-09-14 | Monsanto Res Corp | Polymeric polyisocyanurate laminating resin prepared from a diaryl dhsocyanate and acocatalyst system |
| US3211703A (en) * | 1962-03-23 | 1965-10-12 | Monsanto Res Corp | Polyaliphatic polyisocyanurate laminating resin prepared in the presence of a cocatalyst system |
| US3494888A (en) * | 1966-08-30 | 1970-02-10 | Wilbur R Mcelroy | Resin compositions from polyepoxides and isocyanate polymers |
| US3745133A (en) * | 1968-02-05 | 1973-07-10 | Upjohn Co | Cellular isocyanurate containing polymers |
| US3793236A (en) * | 1971-02-12 | 1974-02-19 | Mitsubishi Chem Ind | Oxazolidone-modified isocyanurate resins |
-
1972
- 1972-11-29 JP JP47118986A patent/JPS5231000B2/ja not_active Expired
-
1973
- 1973-11-23 GB GB5457373A patent/GB1447500A/en not_active Expired
- 1973-11-27 CH CH1661773A patent/CH606170A5/xx not_active IP Right Cessation
- 1973-11-27 AU AU62947/73A patent/AU470978B2/en not_active Expired
- 1973-11-28 FR FR7342337A patent/FR2207952B1/fr not_active Expired
- 1973-11-28 DE DE2359386A patent/DE2359386C3/de not_active Expired
- 1973-11-28 SE SE7316070A patent/SE417977B/xx unknown
- 1973-11-28 CA CA186,866A patent/CA1006293A/en not_active Expired
- 1973-11-28 SU SU1975403A patent/SU525433A3/ru active
- 1973-11-28 NL NL7316281.A patent/NL163539C/xx not_active IP Right Cessation
- 1973-11-28 IN IN2621/CAL/1973A patent/IN140854B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1447500A (en) | 1976-08-25 |
| FR2207952A1 (enrdf_load_stackoverflow) | 1974-06-21 |
| DE2359386A1 (de) | 1974-06-20 |
| JPS4994798A (enrdf_load_stackoverflow) | 1974-09-09 |
| IN140854B (enrdf_load_stackoverflow) | 1977-01-01 |
| NL163539B (nl) | 1980-04-15 |
| NL163539C (nl) | 1980-09-15 |
| DE2359386B2 (de) | 1980-08-07 |
| SU525433A3 (ru) | 1976-08-15 |
| NL7316281A (enrdf_load_stackoverflow) | 1974-05-31 |
| AU6294773A (en) | 1975-05-29 |
| AU470978B2 (en) | 1976-04-08 |
| CH606170A5 (enrdf_load_stackoverflow) | 1978-10-31 |
| CA1006293A (en) | 1977-03-01 |
| SE417977B (sv) | 1981-04-27 |
| JPS5231000B2 (enrdf_load_stackoverflow) | 1977-08-11 |
| FR2207952B1 (enrdf_load_stackoverflow) | 1978-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8281 | Inventor (new situation) |
Free format text: NARAHARA, TOSHIKAZU SUGAWARA, KATUO KARASAWA, YOSHIHARU, HITACHI, JP YOKONO, HITOSHI, KATSUTA, JP MUKAI, JUNJI MUROI, TADASHI, HITACHI, JP |
|
| C3 | Grant after two publication steps (3rd publication) |